(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole → (7bR,11aS)-9-[3-(4-fluoro-2-nitrophenoxy)propyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole

HRID 47539Notes

Reaction equation

HRID 47539 reaction equation
[CH2:1]1[N:12]2[C:13]3[C:9]([C@@H:10]4[CH2:17][NH:16][CH2:15][CH2:14][C@@H:11]42)=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:4][S:3][CH2:2]1.Cl[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[N+:30]([O-:32])=[O:31]>>[F:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:16]2[CH2:15][CH2:14][C@@H:11]3[N:12]4[CH2:1][CH2:2][S:3][CH2:4][C:5]5[CH:6]=[CH:7][CH:8]=[C:9]([C:13]4=5)[C@@H:10]3[CH2:17]2)=[C:24]([N+:30]([O-:32])=[O:31])[CH:25]=1

Participants

3

Reactant 2

HCID 10198786(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indoleHCID 15096971HCID 15096971, compound

Product 1

HCID 60071796(7bR,11aS)-9-[3-(4-fluoro-2-nitrophenoxy)propyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole

Procedure

The title compound of EXAMPLE 6 was prepared from (7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole and and 1-(3-chloropropoxy)-4-fluoro-2-nitrobenzene following the procedure described in EXAMPLE 4. 1H NMR(CDCl3, 300 MHz): δ 7.6 (m, 1H), 7.25 (m, 1H), 7.04 (m, 1H), 6.96 (d, 1H, J=6.6 Hz), 6.92 (d, 1H, J=6.6 Hz), 6.75 (m, 1H), 4.25 (m, 2H),3.82 (m, 2H), 3.59-3.00 (m, 8H), 2.80 (m, 2H), 2.48 (m, 2H), 2.22 (m, 2H), 1.20 (m, 2H) ppm. LRMS (ES)+: 444 (M+H)+.

Sources & evidence

ORD record
ord-bfd70ffb31084752a5866123d2f4ca66
Source dataset
uspto-grants-2004_03
Patent number
US06699852B2

Reaction notes

Loading…